


Late Night at the Office

by beestiels



Category: Supernatural
Genre: Aftercare, Anal Fingering, Anal Sex, BDSM, Bottom Castiel, Bottom!Cas, Comeplay, Coming Untouched, Dirty Talk, Dom Dean, Exhibitionism, M/M, Office Sex, Spanking, Sub Castiel, Top Dean, Top Dean Winchester, Twink Castiel, dom!Dean, hole spanking, sub!cas, top!dean
Language: English
Status: Completed
Published: 2015-02-02
Updated: 2015-02-02
Packaged: 2018-03-10 04:14:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,681
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3276320
Author URL: https://archiveofourown.org/users/beestiels/pseuds/beestiels
Summary: <blockquote class="userstuff">
              <p>Dean Smith rims, spanks, fingers, and fucks Castiel against the big window in his fancy office, late at night after everyone else has left the building.</p>
            </blockquote>





	Late Night at the Office

**Author's Note:**

> **edit: I made a super silly typo and tagged this as "bottom dean" when I meant to type "dom dean" instead. Sorry for any confusion, there is no switching/bottom!Dean in this fic, it's just dom!top!Dean with bottom!sub!Cas.**
> 
>  
> 
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> 
> Originally posted to [my tumblr](http://beestiels.tumblr.com/post/106492472043/dean-smith-fucks-twink-cas-against-the-big-window) on Dec 29th, 2014.
> 
> I'm still getting used to AO3's tagging system, forgive me. The spellings of the popular tags here a bit different from tumblr's with some things (I'm so used to tagging "twink!Cas" on tumblr... apparently it's just "twink castiel" here. I'll have to go back to fix some of my previous posts.)
> 
> Also, I hope it's okay that I'm using both the Dean Winchester and Dean Smith tags here, and both the Castiel/Dean Winchester and Castiel/Dean Smith tags since I'm not really sure how it works or what the curtesy is? But generally when I write Dean Smith, it's just so I can kinda have an excuse to make Dean rich with a fancy loft and fancy office and be with twink!Cas haha, so his personality is a bit more on the Dean Winchester side. Though really, I feel like Dean Smith's personalities in It's A Terrible Life are very much part of the "real" Dean's personalities, just maybe stuff he tends to repress because of his hunter lifestyle. ANYWAY sorry for rambling.
> 
> Okay it's 4:30 am so I'm gonna get some sleep before I put the rest of my fics on here.

Castiel Novak was getting to know the thick, sturdy, wrap-around glass window in Dean Smith’s office quite intimately. Currently, he was specifically getting to know its soothing, cooling effect on his front while the rest of his body was burning from being thoroughly tongue-fucked by the man who owned the office said window was located in.

It was a couple hours after everyone else had gone home, no one else in the sleek, corporate building, and Dean hadn’t bothered to shut off any of the warm white lights in his luxurious executive office. Anyone in any of the nearby buildings at their height was sure to be able to see straight inside, and that knowledge coupled with the sloppy sounds of Dean’s supple lips and soft tongue lavishing over his sensitive hole had Castiel’s cheeks flaming hotter with excitement and his cock dripping precome onto the smooth glass.

An empty feeling overwhelmed him and his backside felt significantly cooler as Dean pulled away, and Cas whimpered at the loss. Despite his disappointment, he still kept his hands firmly in place where Dean had told him to: spreading the firm globes of his ass apart for Dean’s viewing delight, as well as for making it easier to rim him. A sharp stinging slap against his hole shocked him into a full-body twitch, and he almost came immediately, barely holding back, as Dean hadn’t given him permission for release yet.

"You’ve got such a pretty hole." Dean praised just before giving it another teasing slap.

Castiel keened and arched his spine, pressing his front harder against the glass, the coolness making his nipples go erect. He knew that Dean was aware not much more set him off quite liked getting his hole spanked –his dom wasn’t going to make it too easy for him not to come tonight.

“Like that, sweetheart?” Another spank. “Bet you look so pretty from the front right now, blushing like a little slut. I bet everyone else looking at you right now thinks the same thing. They probably wish they were me.” Another slap. “I mean, who wouldn’t want this sweet little hole of yours? And your cock always looks so pretty when you’re dripping and trying not to come.”

“Sir, please.” Castiel panted.

“Please what?”

“More, more.” 

Dean imagined Castiel’s eyes would be murderous if he could see the smug smirk on his face right now. “More what, sweetheart? I want to help you, but you have to be more specific.” He barely bit back a snicker, green eyes twinkling with mirth.

“I want you,” Castiel gulped. He was stark nude, hard, and leaking in a fully lit room pressed against a floor-to-ceiling window in a busy city without shame, yet he was fighting embarrassment in vocalizing to his lover what he wanted. He swallowed again. Dean wouldn’t make him feel embarrassed. He would respect Cas no matter what he asked during their scenes, and remembering that gave Castiel the resolve he needed. “I want you to spank my hole more, Sir, then fuck me until I come untouched against the window, please.”

Dean moaned at Castiel’s words. “You like everyone watching what a little slut you are? Happy that they’ll see what a good boy you are when you come without me touching your cock?”

“Yes, Sir.” Castiel answered breathlessly as Dean slapped his hole twice more.

“Such a good little whore. Gonna get your slutty hole all sensitive from a good spanking, them I’m gonna fuck you till you scream.” He rained down several more sharp slaps consecutively, then rubbed the quivering rim with soothing motions.

“Brace your hands on the window, sweetheart.” Dean instructed gently as he grabbed the bottle of lube that was beside him on the floor. He had placed it there at the beginning of their scene, knowing he’d be too excited to want to retrieve it from his desk. “Now, ask nicely for my fingers.”

“Please,” Cas complied, “please, Sir, want your fingers in me. It feels so good when you put them in them in me. They’re so thick and strong. I’ve been wanting your fingers in me all day.”

“I’ll bet you have, with the way you’ve been moaning like a little bitch for me all night.” 

The sound of the slippery liquid being squeezed out of the tube caused Castiel to shiver with anticipation. He tried to relax, and shifted his position slightly to drop his shoulders and keep his body bent a bit lower to make this part easier on the both of them. Luckily, Castiel’s hole was already partially open and wet from the long rimming session, and the slim plug he had been wearing beforehand. It had been his smallest one though –Dean wanted to be able to enjoy opening Castiel up, and hadn’t been in the mood for a toy to do all the work for him that day.

A sigh of relief filled the air as Castiel felt Dean’s index finger slip into him to the second knuckle, then slowly to the hilt. Dean had coated his fingers with a generous amount of lube, and between that, the plug, and the rimming, Castiel’s body accepted the first finger easily despite how wide Dean’s fingers were.

“There you go angel, doing so good for me. Maybe next time we’ll do this facing the other way, so everyone out there can see your pretty hole too. Would you like that?”

“Yes, Sir.” Castiel breathed, his cock jumping at the tought.

Dean noticed a shiny string of precome slip down the window and smiled, proud he had such an affect on his sub with just his words and a single digit.

Dean worked his finger in and out slowly. He knew Castiel could take more movement, but he wasn’t above teasing. He crooked and curled his finger a bit, and purposely avoided Castiel’s prostate. He’d wait until the second finger for that. Instead, he cruelly teased just slightly below where he knew the sweet spot was. He heard Castiel mewl in frustration, and finally started to take some pity.

“Ready for another?” Though he already knew the answer.

“Yes, please, Sir.”

“Such a polite boy.” Dean admired as he slipped his middle finger in slowly.

With his other hand, he dripped just a bit more lube over Castiel’s hole, and Castiel shuddered at the cool slickness running down him. It was actually too much lube, and Dean knew it, but he loved seeing Cas so wet between his young, athletic thighs.

“Dripping like a good little bitch.” He remarked. “Your thighs are so wet. I can’t wait to get you even messier for everyone to see.” 

With that, Dean went relentlessly after Cas’s sensitive spot, rubbing his two fingers against it insistently until his sub was writhing and sobbing with pleasure, a light pink flush spreading down his flexible spine as he arched his back even more. Castiel hissed, and Dean knew his boy’s sensitive nipples must be pressing against the cool glass window, and absently wished Castiel were facing his way so he could play with them. He’d save that for another time, though. For now, he relished in the way Castiel circled and bucked his hips back against his fingers, whimpering and begging for another, which Dean was happy to give him. The digit went in easily and Castiel shouted in rapture loud enough that, had it still been working hours, his assistant surely would have been able to hear him from outside the door.

“So eager. Your slutty hole lets me in so easy. Probably because it wants my big cock so bad.” He pet Castiel’s trim sides soothingly as he worked his fingers in his hole, curling and spreading and scissoring.

Dean pulled his fingers out all too soon, and Cas let out a loud, drawn-out whine.

“Shhhhh, angel.” He soothed. “Just getting my cock ready for you.”

Dean squirted more lube on his hand and stroked his throbbing cock perfunctorily. The pressure was nice, but he wanted all his gratification to come from Castiel’s ass tonight, so he kept his movements strictly to lubing himself up, and staved off pleasuring himself. As a distraction, he watched the way Castiel’s now dark pink hole fluttered and clenched around nothing, desperate to be filled again, with something more than just a few fingers. He focused on the way the aroused, pink flush had crept down Castiel’s entire back, and how sex gave Castiel’s smooth skin a golden glow, highlighted by the night time city lights the open window allowed them to see.

“Wish you could see yourself, Cas.” Dean was more than done lubing himself up, but he wanted to rile Castiel up a bit more with his words before fucking him. “Your hole’s so open for me. It’s twitching because it wants my cock so bad. God, you look like such a desperate little whore, bent over, all wet between your legs like a bitch in heat, waiting for my big cock to fuck your twinky little ass.” 

Castiel moaned low in his throat, and Dean caught the glimmer of another blurt of precome rolling down the window.

“And showing off for everyone out there the whole time too, showing off what a good boy you are. The perfect, pretty little cockslut.”

Dean walked up to Cas and steadied him with a hand on one of his sharp hipbones, the other gripping the base of his cock. No matter how open Cas was, Dean would always make sure to carefully guide himself in. The last thing he wanted to do was hurt him on accident.

“Ready for my cock, angel?”

Castiel bit his lip cherry red to calm himself before responding. “Yes, Sir, please, make me scream.”

In one smooth motion, Dean did just that. Castiel cried out in ecstasy at being filled all at once, and looked back at Dean with lust burning in his bright blue eyes. Dean captured Castiel’s plump, chapped lips in a rough kiss and began vigorously fucking him against the window, eternally grateful that he worked for a billion-dollar company with glass sturdier than most people’s brick walls. Fulfilling Castiel’s exhibitionism kink solely at their upper floor loft would have been fine with the both of them, but they liked having the option to be able to switch it up.

Throaty groans and slick sounds filled the air as Dean pounded Cas relentlessly into the window, kissing and biting along Cas’s shoulders, and placing his hands on top of Castiel’s where they were braced against the window, lacing their fingers together. He remembered his sub’s request from earlier, and kept his hands clear of his cock. He knew Castiel could do it; it was fairly easy for Castiel to come untouched now, especially from all the training sessions they’d had to be able to get him to do it regularly after he did it once on accident and enjoyed it so much that Dean thought he’d never be able to roll Cas out of bed again.

“Sir,” Cas managed to find words through his haze of desire, “fuck me harder, please, fuck me harder.” 

“Such a fucking cockslut.” Dean grunted as he quickened his pace.

Dean thrust into Cas as deep as he could several times in succession, then kept his hips flush against Cas’s ass as he ground circles against his prostate, Cas’s body pressed all the way up against the window, his cock trapped between his body and the glass. The sub was letting out loud, pathetic whimpers at the constant attention to his prostate, his breath coming short and quick, moans, curses ,and “please sir,”s “more sir,”s “love your cock sir”s spilling from his kissed-bruised lips in his sex-rough voice.

Dean worked his hands away from Cas’s and wedged them between his lithe chest and the glass to tweak, rub, and pinch his nipples, which he knew must be red and sensitive from pressing against the stiff glass so much by now. The added stimulation had Cas shaking and shouting his bliss.

“Sir, please, Sir, I have to come, please.” He begged.

“Shhh, it’s okay angel, you can come whenever you want now. Come for me.”

Dean’s permission was all it took, and Castiel was tumbling over the edge. His released gushed out hot and thick onto the glass, his body twitching and hole fluttering around Dean’s cock as the older man fucked him through his orgasm. Castiel’s hole spasming around Dean’s cock through his release increased the delicious pressure around Dean’s length –he just felt so tight when he was coming –and Dean was following soon after, his cock pulsating and come flooding Castiel’s hole, already so full with the extra lube that his release began dripping out and down Castiel’s thighs in the midst of his orgasm, creating the erotic mess Dean had been wishing for from the beginning. He pulled out carefully and ran his fingers through the creamy wetness, gently petting Castiel’s over stimulated entrance and scooping some of the come and lube back in.

“Such a sloppy, sweet slut for me, angel.” He cooed.

They came down from their highs slowly, and Dean reflexively wrapped his strong, freckled forearms around Castiel’s middle as he felt him slumping down against the window. He guided the tired twink to his large office couch, and laid him down gently.

“I’ll be right back.” He promised with a kiss to Castiel’s sweaty, flushed forehead.

Dean trotted quickly to his office mini fridge and grabbed two bottles of grape juice, then plucked the bags of trail mix off his desk. He twisted the cap off one bottle as he headed back towards Cas, and he lifted his head off the couch pillow as he saw Dean come back, ready to take a few sips of the refreshing liquid. Dean tipped the bottle to Castiel’s lips for him. Castiel could probably do that himself, but Dean liked to take care of him as much as possible after a scene. He knew how important the aftercare was, and he didn’t want Castiel to have to do anything that he couldn’t do for him.

“You were so good for me.” He petted through Castiel’s dark, damp hair as he took slow sips of the fruit juice. “You took everything I gave you so beautifully, I’m so proud of you.”

Castiel pulled his mouth off the bottle and Dean twisted the cap back on, kissing one of Castiel’s pink cheeks as he opened and handed Cas a bag of trail mix. Cas smiled when he saw it was one of the ones with banana chips in them.

“Thank you.” He nodded and began crunching away.

“You’re welcome, sweetheart. I’ll cuddle with you and let you rest a little more. Then I’m going to stay here, but I’m going to have to get off the couch and clean up our mess, okay?” He began rubbing Cas’s thighs, which he knew must have been sore from holding himself up for so long.

Castiel nodded. “Okay. I’ll be fine while you clean up, Dean. I know you’re not leaving me.”

“Good.” Dean gave him another kiss on the cheek. “Then I’ll walk us to my car, and we can go home and eat dinner and take a bath or shower, whichever you want. You did so good holding yourself against the window the whole time,” he praised again, “I know that must’ve been hard and made you tired. I’ll give you a massage in bed after we clean ourselves up, and we’ll do whatever you want the for rest of the night.”

“I want to watch the documentary on bumble bees I have sitting on the DVR.” Castiel yawned and took another bite of his trail mix and washed it down with more juice.

“Of course you do.” Dean laughed. “We can do that, Cas. Like I said, whatever you want.”

He opened his own bottle of grape juice and nuzzled into his boyfriend, looking forward to the relaxing night they had together ahead of them.


End file.
